Process of developing photographic materials and new photographic developers



Patented May 13, 1930 UNITED STATES PATENT: orrrcr Gus'rav RELDDELIEN Am) wnmmn MULLER, or LErrzIe; Germany, assrenons, BY

unsnn assrenmnn'rs, 'ro AGFA Ansco conrom'rron, or nmerrmron, NEW

YORK, A CORPORATION OF NEW YORK PROCESS OF DEVELOPING PHOTOGRAPHIC MATERIALS AND NEW PHOTOGRAPHIC DEVELOPERS No Drawing. Application filed li'ovember 2, 1927, Serial No. 230,687, and in Germany November 19, 1926.

The present invention relates to a process of developing photographic materials and to new photographic developers, more-pap ticularly to the photographic developers comprlsing as developing agent a compound 6f the general formula:

wherein X represents hydrogen or the group It is known that 4-amino-1-hydroxybenzene and its N-mono-alkylated derivatives are developers of the latent photographic image in, silver halide layers. Qf the" twice N-substit'uted 4 amino 1 hydroxybenzenes only 4-11 droxyphenyl-N-alkylglycines have hitherto been known as photographic developers.

Now we have found that the 4-hydro2 zyethylamino-l-hydroxybenzene and the 4-di- 'hydroxyethylamino--1 -hydroxybenzene are I particularly suited, for the use as photographic developers. Both compounds were hitherto unknown, the manufacture" of them has been described in our Patent Number 1,712,716, dated May 14, 1929, and consists in the'condensation of 4-amino-l-hydroxybenzene with a halogenhydrin of glycol.

A suitable developer consists of a solution of 1 ram of 4-dihydroxyethylamino-1-hy droxy enzene in.200 cc. of water-with 10 grams of crystallized sodium sulphite, 10

grams of potassium carbonate and 0.05 gram of otassium bromide. It develops just as a eveloper does from 4-amino-1-hydroxybenzene as developing agent but it is of more advantageous composition and of normal concentratiorn The chief advantage is that the new developing agent is permanent in 200 cc. of water with 20 grams of crystallized sodium sulphi'te and 5 grams of potassium carbonate develops more strongly than those made from normal 4-amino-1-hydroxybenzene developers. The new developer exc'els the best of the hitherto known developers in that it is extraordinarily soluble, is remarkably permanent even in alkaline solutions and, what is of particular advantage, develops completely without fog, even in so- *lution free from potassium bromide.

\Vhat we claim is 1. A photographic developer containing together with other developer ingredients-a compound of the general formula:

wherein X represents a substituent of the group consisting of 2. A photographic developer containing together with other developer ingredients 4 hydroxyethylamino-l-hydroxybenzene.

3. A photographic developer comprising an alkaline solution containing sodium sulfite and a compound of the general formula:

5 -O dmcmon wherein X represents a substituent of the group-'consisting of 4 "'-H and' '-oH,.oH2.oH. 6. A photographiodeveloper comprising an alkaline solution containing sodium sulsodium sulfite and a compound of the g neral formula;

fite and 4-hydroxyethylamino-l-hydroxybenzene.

7. A photographic developer comprising sodium sulfite potassium carbonate and a 5 compound of the general formula:

HO N

crnomoH wherein X represents a substituent of the group consisting of H and -cH..cH.'.oH.

8. A photographic developer comprising sodium sulfite, potassium carbonate and .L-hydroxyethylamino-l-hydroxybenzene.

9. A photographic developer comprising sodium sulfite, potassium carbonate, potassium bromide and a compound of the general,

formula wherein X represents a substituent of the group consisting of H and CH .CH .-OH.

10. A photographic developer comprising sodium sulfite, potassium carbonate, potassium bromide and 4-hydroxyethylamino-1- hydroxybenzene.

11. The process of developing photographic materials which comprises treating the same with a solution containing a compound of the general formula:

\crnomon. I

of the general formula:

HO N X onionion x wherein X represents a substituent of the group consisting of 3 H and. '-CH .CH2.OH.

14. The process of developing photographic materials which comprises treating the same with a solution containing together with other developer ingredients 4-hydroxyethylamino-l-hydroxybenzene.

15. The process of' developing graphic materials which comprises treating the same with a solution containing sodium photo sulfite and a compound of the general formula . X no N l O omcmon wherein X represents a substituent of the group consisting of H and CH .CH .OH.

16. The process of developing photographic materials which comprises treating the same with a solution containing sodiumsulfite and l-hydroxyethylamino-1-hydroxybenzene.

17. The process of developing photographic materials which comprises treating the same with an alkaline solution containing sodium sulfite and a compound of the general formula cmomon wherein X represents a substituent of the g'IOlgl P consisting of --H and CI I2-CHg-OH- The process of developing photographic materials which comprises treating the same with an alkaline solution containing sodium sulfite and 4-hydroxyethylamino-1- hydroxybenzene.

' 19. The process of developing photographic materials which comprises treating the same with a solution containing sodium sulfite, potassium carbonate and a compound of the general formula:

no N\ cniomon wherein X represents a substituent of the .group consisting of 20. The process of developing photographic materials which comprises treating the same with 'a solution containingsodium sulfite, potassium carbonate and 4 hydroxyethylamino-l-hydroxybenzene.

21. The pro ess of developing photographic materia s which comprises treating the same. with a solution containing sodium su'lfite, potassium carbonate, potassium bromide and a-compound of the general. formula 1 no N X omomon group consisting of -H and CH .CH .OH.

' wherein'X represents asubstituent of the 22. The process of developing photographicmaterials which comprises treating the same with a soliition containing sodium.

sulfite, potassium carbonate, potassium bromide' and 4-h'ydroxyethylamino-l-hydroxybenzene. g

Intestimony whereof, we aflix our signatures.

GUSTAV REDDELIEN. I WERNER MULLER. 

